Caramelized pineapple upside-down cake with maraschino cherries is a retro family dessert showstopper. This stunning, single-layer cake features a beautiful fruit topping that's baked right in.
Preheat oven to 350°F (175°C). Melt 1/4 cup butter and pour into a 9-inch round cake pan, tipping to coat the bottom evenly.
Sprinkle 1/2 cup packed brown sugar over the melted butter, spreading evenly. Arrange pineapple rings decoratively in the sugar layer and place a cherry in the center of each ring.
In a medium bowl, whisk together flour, baking powder, and salt for even leavening. In a separate large bowl, cream 1/4 cup softened butter with 1 cup sugar until fluffy. Beat in eggs one at a time, mixing thoroughly after each.
Blend in vanilla extract. Alternate adding the flour mixture and milk to the creamed mixture, starting and ending with flour. Mix until just combined—do not over-mix.
Spoon the batter gently over the fruit layer and spread evenly to edges with a spatula. Bake at the center rack for 40–45 minutes, until a tester inserted into the center of the cake comes out clean and the edges are golden.
Remove from oven and let the cake rest in the pan for exactly 5 minutes—no longer, to prevent sticking. Loosen edges with a knife then confidently invert onto a serving platter while the topping is still hot for a glossy finish.